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The crystal and molecular structure of 5‐ N ‐methyl‐β‐d‐arabinofurano[1′,2′:4,5]oxazolo‐ S ‐triazine‐4,6‐dione: Molecular modeling studies on the pattern of alkylation of β‐D‐arabinofurano[1′,2′:4,5]oxazolo‐ s ‐triazin‐4‐one‐6‐thione
Author(s) -
Purkayastha Subhasish,
Cheer Clair J.,
Panzica Raymond P.
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270351
Subject(s) - chemistry , intramolecular force , adduct , covalent bond , triazine , alkyl , crystal structure , stereochemistry , solid state , alkylation , molecular model , molecule , crystallography , computational chemistry , polymer chemistry , organic chemistry , catalysis
The involvement of the 5′‐hydroxyl group on β‐D‐arabinofurano[1′,2′:4,5]oxazolo‐ s ‐triazin‐4‐one‐6‐thione ( 1b ), to form an intramolecular covalent adduct at C6, is postulated to explain the formation of almost equal amounts of 5‐ N ‐alkyl‐β‐D‐arabinofurano[1′,2′:4,5]oxazolo‐s‐triazin‐4‐one‐6‐thione and 5‐ N ‐alkyl‐β‐D‐arabinofurano[1′,2′:4,5]oxazolo‐ s ‐triazine‐4,6‐dione during alkylation of 1b . An X‐ray crystallographic study was conducted on 5‐ N ‐methyl‐β‐D‐arabinofurano[1′,2′:4,5]oxazolo‐ s ‐triazine‐4,6‐dione ( 2a ) and its solid state structure was established. This was compared to the energy minimized structure of the same compound that was generated by the molecular modeling program, MACROMODEL. Force field calculations (Allinger's MM2) on this structure and other intermediates lend support to the concept of formation of the intramolecular covalent adduct.